Qohelet 7:25-8:1 contains one of the most troubling passages in the Hebrew Bible, where the speaker presents women as more bitter than death and associates them with deception and danger. This study asks whether—and how—such an explicitly misogynistic text can still matter today without being either excused or dismissed. Rather than attempting to rehabilitate the passage ethically, the paper situates it within the literary strategy of Qohelet as a whole, arguing that its gendered polemic functions rhetorically to expose the limits of wisdom, experience, and moral generalization. The passage is read against the backdrop of ancient Near Eastern wisdom traditions, where personified Woman—both positive and negative—serves as a symbolic device rather than a sociological description. At the same time, the paper takes seriously the historical and contemporary harm caused by such language, especially in interpretive communities that have read it prescriptively. By distinguishing between descriptive rhetoric, ideological critique, and reception history, the study proposes a hermeneutical framework that allows the text to be engaged critically: not as a timeless norm, but as a witness to the tensions, failures, and contradictions internal to biblical wisdom itself. In this way, Qohelet 7:25-8:1 remains relevant—not because it offers ethical guidance, but because it forces readers to confront the fragility of wisdom claims and the responsibility of interpretation in the face of problematic scripture.